Best price vacation rentals in Upper Sugarloaf Key, FL 33042, USA • 133 Listings
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Upper Sugarloaf Key, FL 33042, USA Vacation Rentals | 

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5.0 (2)
Brand New Modern Ocean Front Luxury Home
Up to 8 guests
Airbnb$900
Vrbo$914
Average Nightly Rate
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5.0 (12)
Luxurious Oceanfront Home w/ a Private Pool, High-speed Wifi, & Private Beach
Up to 8 guests
Vrbo$2,159
Airbnb$2,637
Average Nightly Rate
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5.0 (2)
Dazzling Bayfront Home w/ 2 Boat Docks, Huge Deck, 1 Kayak, Pool Table -1 Dog OK
Up to 6 guests
Vrbo$220
Airbnb$273
Average Nightly Rate
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5.0 (20)
Vacation like a local
Up to 8 guests
Airbnb$375
Vrbo$375
Average Nightly Rate
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5.0 (12)
New 3 Bedroom,2 Bath house 60ft dock Two Minutes from Kemp Channel
Up to 8 guests
Airbnb$140
Vrbo$140
Average Nightly Rate
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5.0 (92)
Blue Vacation Home. Private heated pool.
Up to 8 guests
Vrbo$475
Airbnb$520
Average Nightly Rate
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4.9 (33)
Canal Front, Spa/Pool, 2 Kayaks, 2 Bikes, 3 Bed, 2 Bath, Oceanside Home
Up to 5 guests
Airbnb$198
Vrbo$198
Average Nightly Rate

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4.9 (158)
White Vacation Home, read our reviews. Private dock, private heated POOl.
Up to 8 guests
Vrbo$500
Airbnb$570
Average Nightly Rate
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4.9 (62)
Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!
Up to 12 guests
Airbnb$639
Vrbo$639
Average Nightly Rate

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4.9 (125)
Oceanfront house with private pool
Up to 9 guests
Vrbo$500
Airbnb$565
Average Nightly Rate
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4.8 (53)
Private pool, spectacular views & dock
Up to 12 guests
Vrbo$658
Airbnb$665
Average Nightly Rate
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4.8 (53)
Private home in the keys -POOL-Bikes-Kayaks Special pricing SAVE!
Up to 6 guests
Vrbo$275
Airbnb$294
Average Nightly Rate
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4.8 (5)
Oceanside, pet friendly, 5/3 smart home with paddle equip.-SUPs, kayaks & canoe
Up to 12 guests
Airbnb$260
Vrbo$280
Average Nightly Rate
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4.7 (11)
Pet friendly amazing location in paradise
Up to 9 guests
Airbnb$225
Vrbo$268
Average Nightly Rate
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4.2 (13)
Extensive Keys House w/ Bikes, Private Pool, Free WiFi, & In-Home Washer/Dryers
Up to 20 guests
Vrbo$2,089
Airbnb$2,155
Average Nightly Rate
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4.0 (1)
BIRDS OF PARADISE - Amazing Sunsets, Open Water Views, Boat Dockage & Dog Fri...
Up to 8 guests
Vrbo$1,000
Airbnb$1,211
Average Nightly Rate
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0.0 (0)
3 bedroom accommodation in Summerland Key
Up to 6 guests
Vrbo$188
Airbnb$196
Average Nightly Rate
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0.0 (0)
Amazing Waterfront Home w/ Private Beach, Dock, Pool, Free WiFi, Outdoor Kitchen
Up to 7 guests
Vrbo$239
Airbnb$346
Average Nightly Rate
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0.0 (0)
THE BLUE PEARL - Huge Open Water Home, Amazing Sunsets, Boat Bar & Room For T...
Up to 12 guests
Vrbo$454
Airbnb$550
Average Nightly Rate
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0.0 (0)
Dog-Friendly, Canal-Front Home w/Free WiFi, Central AC, Private W/D, Boat Access
Up to 6 guests
Airbnb$169
Vrbo$177
Average Nightly Rate
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0.0 (0)
NEW! Oceanfront Sugarloaf Key Home w/ Private Dock
Up to 8 guests
Airbnb$186
Vrbo$913
Average Nightly Rate
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0.0 (0)
2 Bd/1 Bth Pet Friendly, Furnished Canal House w/ Cudjoe Bay View. 28 Day Min.
Up to 6 guests
Airbnb$210
Vrbo$210
Average Nightly Rate
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0.0 (0)
Waterfront Home w/ WiFi, Private Washer/Dryer, Firepit and Private Gas Grill
Up to 8 guests
Vrbo$331
Airbnb$399
Average Nightly Rate
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0.0 (0)
New Listing! CASA ROSADA - Charming Canal Front Home, Pool, Tiki, Dockage & Q...
Up to 6 guests
Vrbo$374
Airbnb$453
Average Nightly Rate
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0.0 (0)
THE SALTY SAILFISH - Live the Keys Life, Beautiful Canal Front Home, Dockage ...
Up to 8 guests
Vrbo$376
Airbnb$455
Average Nightly Rate
  1. United States
  2. Florida
  3. Upper Sugarloaf Key Vacation Rental Price Comparison

Compare Airbnb vs. Booking.com vs. Vrbo prices for vacation rentals in Upper Sugarloaf Key, FL 33042, USA

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